Potassium Hydroxide → HCID 86741891, compound

HRID 1381659Notes

Reaction equation

HRID 1381659 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[C:4]([C:15]([O:17]C)=[O:16])=[CH:3][CH:2]=1.[OH-].[K+]>CO>[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[C:4]([C:15]([OH:17])=[O:16])=[CH:3][CH:2]=1.[CH2:5]([O:6][CH2:7][CH3:8])[CH3:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 14031270Methyl 10H-phenoxazine-4-carboxylate

Product 1

HCID 86741891HCID 86741891, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl phenoxazine-4-carboxylate (0.241 g, 1 mmol) in methanol (25 ml) containing potassium hydroxide (0.560 g) was heated at reflux for 1 hour. The solvent was removed in vacuo and 5% hydrochloric acid added to the residue. The product was extracted with ethyl acetate, washed with water, dried over sodium sulfate and the solvent removed under reduced pressure. The solid residue was homogeneous by TLC over silica gel (ethyl acetate:hexane 1:3) and was different from the monocarboxylic acid described by Gilman and Moore. After recrystallization from benzene:ethyl ether phenoxazine-4-carboxylic acid, mp 181°-182° C. was obtained.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. customThe solvent was removed in vacuo and 5% hydrochloric acid
  4. additionadded to the residue
  5. extractionThe product was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customthe solvent removed under reduced pressure
  9. customAfter recrystallization from benzene

Sources & evidence

ORD record
ord-5e6fc6ab1eb14c73b7e96af69a01c510
Source dataset
uspto-grants-1989_02
Patent number
US04803269

Reaction notes

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